Conversion of 5-methyl-4H-benzo[d][1,3]dioxin-4-one derivatives into functionalized 8-hydroxyisochroman-1-one under basic conditions

Abstract

Syntheses of 8-hydroxyisochroman-1-one derivatives are described, promoted via a base-induced anionic accelerated rearrangement reaction from dimethyl dioxinone protected resorcylates. A biomimetic polyketide aromatization strategy via selective C-acylation of a β-keto ester, Pd(0)-catalyzed allylic migration and base-promoted cyclization and aromatization furnished the arene core of the resorcylate precursors.